Jake was born in Evanston, Chicago to a single mother. He grew up as a fan of the Second City improv, a comedy theater company based in Chicago that featured comedic talent such as John Belushi and Dan Akroyd.

After graduating from New Trier High School, Jake went on to attend the University of Iowa. During this time, he wrote a play that earned him a spot at NYU’s prestigious Tisch School of the Arts. His play, Cousins, went on to be produced by the Ensemble Studio Theater, an off-Broadway New York group.

While studying at NYU, Jake helped start the sketch comedy troupe known as The Midwesterners. Consisting of Jake and his fellow Midwest peers, the group took their shows on tour around the country.

In addition, Jake also worked with the comedy company Upright Citizens Brigade and performed at Second City’s L.A. venue.

Jake made his screen acting debut in 2006 with small roles in various TV shows and shorts. A year later, he received a six-episode arc on Derek and Simon: The Show. In the next few years, he continued to book guest starring roles on television shows such as Curb Your Enthusiasm, Life to Me, The Unit, FlashForward and Drunk History.

In 2011, Jake finally got the biggest break of his career with a regular role in Fox's comedy New Girl as the love interest of Zooey Deschanel’s character. The show debuted with massive success, garnering multiple Emmy and Golden Globe nominations.

In 2012, Jake starred alongside Aubrey Plaza and Mark Duplass in the indie film Safety Not Guaranteed. The film follows three magazine employees who interview a man who placed a classified ad seeking a companion for time travel. When it premiered at the Sundance Film Festival, it was nominated for the Grand Jury Prize and took home the Waldo Salt Screenwriting Award.